First Dates
by LoveHappyEndings
Summary: She's faced Regina, back in the days where poisoning her with an apple tart was normal, Pan and the Wicked Witch of the West. (Plus the flying monkeys.) She's gone back in time, held someone she loved as he died, and broke a curse. So why does this make her palms sweat as much as those things had?
1. First Dates

**Got a prompt on tumblr, it's on my blog and here.**

**Disclaimer: Don't own these characters**

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It's only been five minutes, yet she's walked out of Granny's a total of seven times, and walked back in a total of six times.

She's faced Regina, back in the days where poisoning her with an apple tart was okay, Pan and the Wicked Witch of the West.

(Plus the flying monkeys.)

She's gone back in time, held someone she loved as he died, and broke a curse.

So why does _this_ make her palms sweat as much as those things had?

It's just a stupid date. A stupid date that's just getting drinks at Granny's. Not even a dinner!

_A first date,_ the equally stupid voice in her head whispers, and she fights the urge to slap her forehead. It's been a while since she's gone on a first date with someone, and Walsh does _not_ count. It's as if she's a teen all over again, and those are days she doesn't want to remember.

She's currently huddled in her car, a watchful eye on the door of the diner in case he arrives. _He's the one who's late,_ the voice supplies. _Maybe he was joking._

But the kisses and _as you wish_ run through her mind, and she knows it wasn't some prank when he asked her on the date. The voice asks if maybe her response to him had made him back out. Emma runs through the conversation and yeah, maybe her actions hadn't really been what they should have been.

_He had managed to sputter out "I've just been taught what a date is..."_

_Her, "and...?" probably had not helped him feel anymore confident._

_"And I'm trying to bloody ask you out on one!" Was his indignant reply._

_Maybe her mouth dropping open hadn't helped either._

_"A date?"_

_"Well, we did just kiss. A date is apparently supposed to happen first." He shrugs and Emma really wants to know who's told him this._

_"Who told you this?"_

_"Henry."_

_Emma's mouth could not drop open anymore. "Henry?"_

_"He says he's a 'Captain Swan' shipper. I have no idea what that is."_

_"Oh."_

_They were both quiet until Killian said, "so, about the date?"_

_"Oh, yeah sure."_

Aaand that's probably why he's late. Or why he isn't even coming.

Emma groans and bonks her head on the steering wheel. She _had _wanted to go on that date, but her thoughts had been all jumbled and he was a _really_ good kisser and-

**_Knock knock_**

"Huh what?" She lifts her head from the wheel and realizes someone was knocking on the window.

"I was planning on having the date inside, Swan." Killian says, his words muffled by the window.

"Oh, right." She opens the door sheepishly and tries not to blush as his appreciating gaze falls upon her. She hadn't known whether or not to dress up, this being her first _first date_ in a while. It's a red dress that made her think of their time in the past, and Henry convinced her to let her hair down and curl it.

She sees for the first time that he's wearing a _suit._

"Who-how do you know what a suit is?" He just smirks and leads her back into the warm, noisy atmosphere of Granny's. There's one table in the back with actual _linen_ napkins and that's the one they sit at.

"I thought you weren't coming." Emma confesses.

"Oh, I was just er, held up by your son." He scratches the back of his neck, she notices the absence of the hook.

"Henry? What did he do?"

"Your lad said that if I hurt you he'd get your father to beat me up, because your father doesn't like me as much as he does. He also told me to buy you flowers, so I was held up at the florists." He winces, "the man there said I shot his daughter, and refused to sell me the flowers so I went somewhere else." He hands her flowers that were lying on one of the seats, and she takes them in surprise as he pulls out her chair, then sits in his own.

"Oh, thank you." She tries to resist the urge to bury her nose in them and smell, the floral scent gently drifts to her nose anyways.

Ruby interrupts their conversation with a "what can I get for you two?" and a muttered, "besides a room at Granny's."

"Just the usual." Emma says, reluctantly lifting her eyes from his blue ones.

"Rum."

"We don't have that."

"...water."

Ruby walks away, but not after looking over at Emma with a wink.

The two sit in awkward silence.

_cricket_

_cricket_

"How badly do you want rum?" Emma asks, hand reaching into her handbag slowly.

"Bloody badly." He glares at the counter, as if blaming Ruby for the lack of rum.

"Here." She hands him a tiny flask, that she'd already filled up earlier because she thought she'd need it.

"Well Swan," he takes a swig from it, "you're more a pirate than you think."

"I am not!" Emma ponders for a bit as she takes back the flask and takes a long drink. "I _did _do a lot of looting though..."

"See?"

"But-but not a _lot!" _Emma defends_._ "We looted some stores, tried to pawn off a bunch of watches...that didn't turn out so well..." She admits.

"Let me tell you about _real_ pirate adventures." He announces smugly.

He tells her of drunken nights, deadly fights, of rough storms, and good form. He attempts to tell her of the bar wenches, but she interrupts him hastily, she knows enough about that.

Ruby comes by with the food, and it's only when Emma has to lean back to make room that she realizes she's slowly been leaning towards Killian. He notices too, and smirks at her.

They're silent while they eat, she tries to avoid his gaze. As soon as they're finished however, they talk some more. Emma doesn't think she's talked so much in one sitting.

Granny soon tells them the diner is closing, and not so subtly kicks them out. It probably didn't help that she spied the flask of rum as well.

"Thanks." Emma says quietly as they stand in front of her door. He insisted on seeing her home, and the car ride had been spent in comfortable silent.

"For?"

"The date. The conversation. The beautiful flowers." She unlocks the door and steps inside.

"It was no problem lass." He shuffles his foot.

_cricket_

_cricket_

"Oh screw it." She grabs him by the lapels and kisses him roughly.

This kiss was different than the last, it was all heat and she couldn't help the sigh that escaped her mouth as his teeth gently nibbled her bottom lip.

She really wishes Henry hadn't interrupted them.

"So I take it the date went well?" He asks. They break apart fast, and he's standing there, smugly with his arms crossed.

"It did." Killian touches his own lips softly, almost unconsciously. She pretends to not notice.

"Aren't you going to ask her one another one?" Henry pointedly looks at the two of them.

"Henry!" Emma scolds, but hopes he does ask her.

"Well Swan, I never did exactly ask you last time." He admits.

"Sorry, my reaction wasn't that encouraging." Emma says sheepishly.

"Emma," Henry sneaks away as things look like they're going to get all fairy tale-y. "Would you accompany me on another date? Maybe next weekish?"

She smiles and leans in, "make that tomorrow," and presses her lips to his again.

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	2. Aftermath of the First Date

**Decided to add this to this fic. If it looks familar it's because it's also Aftermath of the First date. Have some humour. (Or my attempt at it.)**

**Disclaimer: OUAT belongs to Adam Horowitz and Eddy Kitsis.**

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_Beep_  
_Beep_  
_Beep_  
_Beep_  
_Beep  
__-  
__-  
__-  
_**_Crash_**

"Uh wha?" Emma lifts her head from a very hard, and very warm pillow.

Aka Killian's chest.

"This-this infernal thing started beeping." He protests, his hand on the alarm clock. Upon further inspection yet still in a sleepy state, Emma sees that he had crushed it with his bare hand.

"Damn that thing was expensive." She notices they're both naked and flushes as last night rushes back to her. Flashes of pleasure and oh god she actually _moaned_ last night?

"Sorry lass." He lifts his hand and brushes a wayward curl from her face.

"Mom! I heard a crash and-oh. I see your date went _really_ well." Henry bursts into the room and upon sensing the mood in the room, abruptly stops.

"Henry!" Emma tugs the blanket up, it had been slowly falling down. "Sorry! I'll make you breakfast in-"

"It's okay, mom. Other mom is taking me out for breakfast at Granny's. You guys can come if you're...ready in ten minutes."

"Great. We'll be ready lad." Killian makes a shooing motion and Henry scuttles out.

"Well, that was embarrassing." Emma slumps back and puts an arm over her eyes, effectively blocking out the light, and Killian's smirking face.

"Come on, we've got ten minutes. And you're driving, I can't stand to listen to the GPS lady." He gets up and Emma peeks out. _Yup_, that is a nice-

"I see you Swan."

"And I see you." She replies cheekily.

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Emma, Killian and Henry are sitting in their booth at Granny's. Henry and Emma are sipping from their hot chocolates and Killian's drinking from Emma's flask. God, and it's only eleven in the morning.

"Miss Swan. We need to discuss something."

The three of them turn as one to see Regina standing in a defensive position, arms crossed.

The Formerly Evil Queen shudders at how creepy that looked.

"Yeah sure." Emma kisses Killian on the cheek quickly and ignores Henry's beam of pride. He insists on saying it was because of his help on their date that they turned out so well.

And he keeps blathering on about 'Captain Swan.'

"Henry has told me some...disturbing news." She says once they've reached the counter. Ruby flashes them a quick smile before helping another customer.

"Oh god." Emma slaps her forehead. "Was he scarred? Did he _sound_ scarred?" Great, she had mentally damaged her son.

"Actually," Regina rolls her eyes in defeat. "He was quite happy to hear how well your date went. He only sounded _microscopically_ disgusted about your state of dress."

Emma breathes a sigh of relief. "Good. I was-"

"But it is irresponsible of you to bring your dates home and _do the deed_ while my son is sleeping a mere few rooms away."

Emma scoffs. "We weren't loud or anything."

"Then obviously one of you was doing something wrong."

The blonde gasps. "Wha-hey! Killian's been around a while, and it _really_ showed last night." She remembers thinking how he could have _possibly_ learned to do that with his-

"It showed his old age you mean? Was he a bit slow? Had trouble getting it u-"

"You know what I meant!" Emma splutters out. "Besides, Henry's told me about Robin and you, you hypocrite."

Cue guilty look.

"That's right sister, you don't have a leg to stand on in this situation." She triumphantly waves a finger in Regina's face. "_And_...apparently you're quite vocal during it."

"Sssh!" Regina looks like she wants to slap a hand over Emma's mouth.

Emma looks like she's more than willing to bite the hand if that happens.

Regina then looks like she regrets bringing up the whole thing.

_Cricket_  
_Cricket_

"I don't blame you though." Emma shrugs. "He's kind of hot."

"I know right?" They're both quiet again, until Regina whispers, "so, is he good with his tongue or no?"

"Regina!" Emma's tone is scandalized.

"What? It's always out there! It's a serious question!"

They both turn to see Killian intently listening to something Henry's saying, tongue between teeth in concentration.

"You got a point. And he is." Emma confides.

"Lass? You about done with Swan?" He calls over and the two of then look at each other guiltily.

"Yes, I think so." The bruntette quickly walks over to the booth, Emma trailing behind. Regina slides in beside Henry and Henry begins to talk animatedly to her.

"What did the Queen need to speak with you about?" He nuzzled her hair affectionally.

"Oh nothing."

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**Reviews are loved!**


	3. Conversations with Henry

**Yes. They are OOC. Especially Henry. But it's funny writing him like this.**

**Disclaimer: I do not own OUAT.**

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"You love my mom." Killian looks up with a start to see Swan's boy sliding into the booth across from him.

"I do." He takes a swig from his flask nervously, and swats away Henry's hand as he does the universal 'gimme the flask' gesture. "And?"

"Well, when you love someone you go on a _date _with them." Henry clasps his hands together and leans forward, speaking softer. Probably because Swan's father is sitting at a table a mere few feet away. And the gossipy waitress keeps wandering over, eavesdropping.

"A date?" He's puzzled.

"Yes. You usually go on one of those _before_ you kiss." Henry sighs exasperatedly.

"We-we didn't!" Killian splutters. The less the lad knows, the better.

"I saw you that night at Granny's. _And_ Grandma told me you did in Neverland. _And_ I bet you did when you went to the past." Henry smirks smugly, and Killian can't help but think it's because of his influence.

"Oh. Well we did kiss." He scratches that spot behind his ear.

"Great. Okay. So what you do is you ask her to go on a date with you."

"How?"

"I don't know. You'll figure it out." Henry shrugs.

"Why are you helping me? Thought you'd want to keep your mother away from a pirate like me." Killian raises an eyebrow.

"You love her. I'm a strong believer in true love. Comes from being in my kind of family." He shrugs again. "I'm also a Captain Swan shipper."

"A _what_?"

"Nevermind. So I'll meet you back at the house after you ask her, then we'll discuss your wardrobe."

"_Wardrobe_?"

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"Lad, what is that?" He points at the outfit laid out on the bed. The two of them are in his room at Regina's.

"It's a suit. It's what formal wear is in this realm." Henry throws the pants at him, then the jacket, then the shirt. Lastly some strip of cloth. "Go change."

He does, and figures the strip of cloth goes around his neck. He ties it in a knot, and almost chokes on it.

It hits him that he did it wrong, as Henry's strangled shriek reaches his ears. He can barely apologize for whatever he did, when Henry's door flies open.

"Henry! What is it?" It's the Evil Queen-er...Regina. Her eyes fall onto him and she giggles. Then laughs so hard she slaps her knee.

Who _does_ that?

"Glad my humiliation is a source of entertainment for you." He says sourly.

"I'm sorry!" She giggles again.

"Someone help! I got this 'date' in less than an hour!" He throws his hands up in the air.

"Well, now you're sounding like a teenage girl." Regina tuts and starts tugging at the cloth. "I don't know what Miss. Swan sees in you."

"My dashing looks help." He supplies as she manages to do whatever it is men do with the cloth.

"FLOWERS!" Henry screeches and looks around wildly as if expecting them to hop out from under the bed with a cheerful, 'we're over here!'. "I forgot the flowers!"

Regina rolls her eyes and calms him down as Killian fidgets with the suit. He's used to low cut necklines, and this..._monkey suit_ is everything he doesn't like. Swan better appreciate it.

"What about that florist? Game of Thorns?" Regina suggests and Henry's eyes light up.

"Yes! Thanks mom!" He grabs a pen and paper and writes something down. "Go here, and buy her flowers. Give them to her at the start of the date."

"Thanks lad." The pirate is touched by Henry's efforts.

"But if you hurt Emma in any way," at this, Henry gets this weird, threatening expression. "I'll get Grandpa to beat you up." While Killian is a little horrified at this, Henry shrugs.

Again.

"I'd do it, but I like you." He pats him on the shoulder and Regina smirks a little. The Evil Queen is probably glad her son has turned out a little like her.

"I won't hurt her." He promises. Then it's off to the florist's. Which as we all know, doesn't go well.

But we also know the date itself, goes _very _well.

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**Reviews are loved!**


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